p-Toluenesulfonic acid → [2-Methyl-3-(pyrazin-2-yl)phenyl]methanol

HRID 2295864Notes

Reaction equation

HRID 2295864 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[N:19][CH:18]=[CH:17][N:16]=2)[C:10]=1[CH3:21].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:21][C:10]1[C:11]([C:15]2[CH:20]=[N:19][CH:18]=[CH:17][N:16]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][OH:7]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 132434252-(2-Methyl-3-{[(oxan-2-yl)oxy]methyl}phenyl)pyrazine

Product 1

HCID 13243426[2-Methyl-3-(pyrazin-2-yl)phenyl]methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.4 g (0.008 mol) of 2-methyl-3-(pyrazinyl)-benzenemethanol tetrahydropyranyl ether and 0.21 g of the pyridinium salt of 4-methylbenzenesulfonic acid in 35 mL of ethanol was warmed to 50° C.±5° C., and stirred for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue stirred for one hour with a mixture of 50 mL of methylene chloride and 50 mL of water. The organic layer was separated, dried, and concentrated under reduced pressure to give 1.6 g 2-methyl-3-(pyrazinyl)phenylmethanol as an oily solid residue.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe residue stirred for one hour with a mixture of 50 mL of methylene chloride and 50 mL of water
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e47948e85af455c958b39c04e31e904
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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